I didn't leave the job, but I had my resignation letter written over this since I would have had to maintain it:

My former boss had an absolute hard-on for "AI" and brought in this low-bid, fly-by-night "AI" software to automate all of our processes. I'm a fan of automation in general, but not this.

This "solution" was basically a glorified macro generator that would screen scrape data from our apps and key into our other apps. Not only it was built on the absolute shakiest platform imaginable, but the documentation from the vendor outright told you to setup remote desktop services in a way that was in violation of licensing in order for it to work. The stack it ran on made a Rube Goldberg machine look like sleek, fine engineering.

I repeatedly told him this was bad software, but he persisted to the point where we nearly went to production with it.

The worst part? The applications he was screen-scraping were all internally-developed. We had access to the backend, frontend, everything. Rather than writing proper processes, he threw that piece of garbage at it.

Luckily he retired before it went to production, and the new CTO shut it the fuck down.

So, I didn't quit my job over it, but I was looking and had my resignation letter written.

Cisco Webex.

You think teams or zoom are annoying? This is much worse. The worst part is with some default meeting settings, a loud chime would play every time someone joined. People kept this on for meetings of 300+ people, then they started talking over the beeps once "the popcorn slowed down."

I hate Teams, give me Slack

Edit: I left an optional team in teams, and still got a notification for a meeting that isn’t on my calendar, my meetings page, nor do I have access to in any other way.

Due to really dumb requirements we had an app that used Python, Visual basic, C and C++, MATLAB, R and JavaScript. I'm not describing an application stack. This was a single binary. The amalgamation was so disturbing that it couldn't even shut down once run, instead asking the operating system to please, please kill me.

Part of the installation procedure involves disabling all SSL certificate verification on company machines.

Didn't leave the job over it, but SAP.

Shitty. Ass. Program.

I’m a camera operator. I work with different cameras on every movie set. The Sony cameras are known to have the worst menu system of all. It’s extremely dense, organized in a manner that makes no sense when on set (the frequently used options are buried in sub menus) and the navigation is painful with a crappy clicky roller. Even the sales rep for Sony openly apologized for the menus. This is unacceptable for a $52,000.00 camera. On the opposite side, there’s ARRI Alexa which has the simplest menu of all. Just a few pages of organized items with simple names. And a lot of common options accessible on the main screen.

Edit:

here’s the Sony Venice menu simulator

And here is the ARRI Alexa menu simulator.

The differences may not be apparent on the simulator but they become critical when on set with a time constraint.

Lotus Notes. I called it Bogus Notes. I do not miss it.

Windows.

I did an internship where my main system was Linux, but it was in a VM on one monitor with the windows host on another for using Windows apps.

Jira. In the Software-as-a-Service world, it's often the tool of choice by Product teams to track issues, by breaking everything down into stories.

It's a horrible, slow, janky mess. The interface is confusing and poorly laid out, you can easily have too many options all over the place, and how its even used can vary dramatically from one company to another.

Salesforce is also trash for very similar reasons. How Sales people around the world all vouched for this thing is beyond me.

ServiceNow. I can't wait to say fuck that SaaS

I left a job over MacOS.

The management was bad. The product was bad. I would have left eventually anyway.

But the constant frustration of using a window manager that does not let you make keyboard shortcuts for most basic window operations, like cycling through windows on the current virtual desktop was too much. And MacOS really does not like you to have multiple monitors in different orientations. There were a whole bunch of other stupid things. I always felt like my computer was fighting me, not working for me.

But on the plus side, it did not have an Ethernet jack, it was really thin so the fans were tiny and made a huge racket, the keyboard sucked to type on, and keys would stop working if a piece of dust with any dimension larger the Plank length got under them.

My last job had not one, but two programming languages they had created in house over the last couple of decades.

One of them was the primary development language for the whole corporation.

Salesforce.

What a fucking piece of shit.

For all the flak it always gets, can I just say I'm relieved nobody said JIRA yet? I think JIRA is great for what to does, but companies are just bad at setting it up right. Either they go overboard with restrictive processes, or they are unorganized mess, there is no in between. But that's not the software's fault. (Braces for downvotes)

Microsoft Windows. I used to be a sysadmin. New job is 100% Linux. Now I never touch Windows unless it's to play a game.

25 yr System Administer who has exited IT: Windows

SAP, closely followed by IBM/Lotus/(I have no idea which random company they were sold to) Notes

I fucking hate this corporate bullshit software

SharePoint

SharePoint

JIRA. Anything made by National Instruments.

Lotus Notes.

Lotus.

I worked for IBM and all out IBM machines had it, but fortunately I did delivery for another major tech client so had a separate laptop and PC for their MS Enterprise environment and 95% of my work was there.

Doesn't matter what job I'm in, Adobe anything is always trash and their seeming monopoly on digital certificate signing in PDFs is disgusting.

SAP

They were transitioning from Oracle SBMS which was bad enough already but SAP... that thing was a nightmare taking dedicated employees (which we didn't have) to account for the additional time needed to enter and manage data

Fortunately I was able to get out before the full switch over; friends that still work there occasionally message to inform how horrible the place has become

I've been in the industry some time but here are some of my most hated software I've been forced to use:

• IBM Clearcase. Absolutely the worst dogshit source control system ever to exist. Complex, fragile, arcane, slow, network intensive. The company had to employ people fulltime on each of its sites whose only job was creating branches and mirroring repos on other sites. The operational & licensing costs of running it must be insane. Some defenders might claim "but it's so powerful!" or "look how we can create fancy layered views" as if that excuses it for being terrible in the most basic ways. Fixing it must have been intractable because IBM Clearcase eventually produced a faster remote client that talked to a proxy of the view running on a server somewhere. More expense and complexity.

• IBM/Lotus Notes & Domino. Another complex, arcane, slow, unintuitive, frustrating product by IBM (though owned by HCL now). Originally a content management system with an email / calendar with its own terminology and workflows completely divorced from any other email / calendar system in existence. Various iterations attempted to rework the front end to appear more user friendly but it was illusory - click button or two and you were confronted with dialogs that hadn't changed in 30 years.

• Internet Explorer. I've worked in company after company that had some really awful in-house expenses system or clock-in/clock-out or some enterprise junk that NEEDED Internet Explorer and no other browser would do because it was so badly written that it couldn't render properly or it used an ActiveX control.

• HP/Microfocus ALM. Another over-engineered, arcane, unintuitive piece of enterprise software. This time for tracking bugs, features, testing etc. Complicated and slow, heavily dependent on Internet Explorer and other deprecated Microsoft tech.

• Trend antivirus. Almost every corporate antivirus is bad but this one has been the bane of my existence. I write code which does stuff like encryption and compression/decompression and this piece of shit would constantly trigger warnings and delete binaries I was trying to build and develop. When it wasn't interfering with my work, it would just be constantly hogging CPU and slowing down disk activity.

• Enterprise software in general. This crap is sold like Kirby vacuum cleaners - a pushy salesman convinces a clueless CTO to buy junk that can seemingly do everything and a sign contract for $$$. And then this stuff is there FOREVER. Management will ignore complaints and the obvious shortcomings of the system because its paid for and the sunk cost fallacy kicks in.

Jira is literally a shiny keychain which keeps PMs distracted and busy enough so that they don't start calling people into a million meetings because they have nothing better to do. It is otherwise completely useless and borderline nonsensical, and any perceived productivity gains from its usage can be attributed directly to keeping superfluous managers away from engineers.

Well nobody mentioned the software I designed, so I'm all good.

Historically, anything that required at least half of an employee to manage.

We're talking SharePoint, exchange, scom, mom. I'll give backup software a pass in general because in the days of tapes, no it's nothing you could do about it but backup exec can f*** right off.

Oracle and a dozen internally developed tools.

Oracle because I'm not an accountant or bookkeeper, but was forced to do a bunch of those tasks anyway.

The internal tools because, while they were "mission critical", they were buggy as hell and there was only a couple of people nationwide who knew how to fix them (or mitigate the damage) when things went wrong.

It's a little thing and I still have to use it, but Cisco Jabber is the most annoying piece of software I have ever used.

It should just boot up and make calls, right? Nope.

It constantly changes the audio output settings dynamically and I can't get it to stick to what I want. Oh, we using the desktop monitor speakers this time the laptop booted up?

It fails to keep credentials and I have to reset it at least once a week.

It does not have a user setting to make it stop taking over as the messaging app. We use Teams for that, which is also pretty crappy but not nearly as annoying as Jabber. Apparently there is a way to address this during installation, but our IT support can't get it to work so I have to manually start up Jabber before Teams because the last one takes over.

Plus all of that is for an occasional phone call that tends to be missed because Jabber decided to forget the credentials again. I have reset Jabber more times than I have received a phone call through Jabber.

Clearcase. Some stone age IBM version control system that predates git.

To ensure there are no conflicts with multiple people working on the same file it relies on locking so only one person can work with the file at a time. Super annoying when people forget to unlock their files after use, which everybody will do.

Very niche. https://en.wikipedia.org/wiki/CityTime_payroll_scandal

NYC GOP Mayor Mike Bloomberg's daughter gifted the City a $65 million boondoggle called 'City Time.' Theoretically, every employee was supposed to scan in with a biometric signature. The software didn't account for things like off site work, shift changes, a 24 hour schedule, etc etc. It would have been simpler just to keep the old paper system and imput everything.

Lotus Notes

Plot twist... my new employer uses it even more 🤦🏻‍♂️

SAP and nearly every accounting package. And I didn't have to use them daily, I just had to support them. Ugh.

I'm a television technical director and Ross Overdrive is hell on wheels... it's a video production system mostly used by local television stations to ~~consolodate~~ "automate" their control rooms down to one person. There's three major companies that build systems like this: Sony, GrassValley, and Ross. In my experience GrassValley's Ignite is pretty good, it's stable and gets the job done. Sony's ELC is best, going above and beyond what I need it to do (plus their customer service and tech people are just awesome). Hands down, Ross Overdrive is a pile of garbage. Their physical video switchers are really great (super intuitive and built to last), but the Overdrive automation system itself is just a clunky and uncooperative UI. I've had such a bad experience with their system I've turned down jobs when the place uses Ross Overdrive. Ross's Xpression graphics system (or "Chyron") is also a hot mess. I've heard that if you're using all Ross stuff (video switchers, graphics system, video servers, robotics, etc) it runs smoothly and that may be true, but Christ-on-a-pogo-stick have I had nothing but trouble with their software.

I'm a sysadmin with a background in computer science, so I'll say any fucking enterprise software on the planet. It's all trash and annoying. I'd run Debian every day of the week over Windows or RHEL and the likes.

I never knew how much I love and appreciate open source/free software until I worked in enterprise...

"But VMWare PERFORMS BETTER than Proxmox!". Yeah, with 10 times the chance of making you depressed.